Methyl 2-formyl-3-(1-methyl-1H-pyrazol-4-yl)propanoate → HCID 178480213, compound

HRID 474570Notes

Reaction equation

HRID 474570 reaction equation
[N+:1]([NH:4][C:5]([NH2:7])=[NH:6])([O-:3])=[O:2].[CH:8]([CH:10]([CH2:15][C:16]1[CH:17]=[N:18][N:19]([CH3:21])[CH:20]=1)[C:11](OC)=O)=[O:9]>C(O)C>[CH3:21][N:19]1[CH:20]=[C:16]([CH2:15][C:10]2[C:8](=[O:9])[N:6]=[C:5]([NH:4][N+:1]([O-:3])=[O:2])[NH:7][CH:11]=2)[CH:17]=[N:18]1

Participants

4

Reactant 2

HCID 18470567Methyl 2-formyl-3-(1-methyl-1H-pyrazol-4-yl)propanoateHCID 86287517Nitroguanidine

Product 1

HCID 178480213HCID 178480213, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To the solution of N-nitroguanidine (912 mg, 8.76 mmol) in ethanol (50.0 mL) was added methyl 2-formyl-3-(1-methyl-1H-pyrazol-4-yl)propanoate (858 mg, 4.38 mmol). It was stirred at 70° C. overnight. After removing the solvent, 10 mL water was added. Then HCl(conc) was added to adjust pH ˜3, and the solution was stirred at 0° C. for 1 h. The solid was collected after filtration. It was dried overnight at 50° C. to get the title compound as an off-white solid (674 mg, 61.5% yield). LCMS: rt=1.17 min, [M+H+]=251.1

Workup

  1. customAfter removing the solvent, 10 mL water
  2. additionwas added
  3. additionThen HCl(conc) was added
  4. stirringthe solution was stirred at 0° C. for 1 h
  5. customThe solid was collected
  6. filtrationafter filtration
  7. customIt was dried overnight at 50° C.

Sources & evidence

ORD record
ord-4c79c7bc4b6e4d4298323cae685077a3
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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